Synthesis of Quinazolinone Derivatives Catalyzed by Triethanolamine/NaCl in Aqueous Media

References

• M. Asif, “Chemical Characteristics, Synthetic Methods, and Biological Potential of Quinazoline and Quinazolinone Derivatives,” International Journal of Medicinal Chemistry 2014, (2014): 1–27.
   Google Scholar
• A. Iwashita, S. Yamazaki, K. Mihara, K. Hattori, H. Yamamoto, J. Ishida, N. Matsuoka, and S. Mutoh, “Neuroprotective Effects of a Novel Poly(ADP-Ribose) Polymerase-1 Inhibitor, 2-{3-[4-(4-Chlorophenyl)-1-piperazinyl] propyl}-4(3H)-quinazolinone (FR255595), in an In Vitro Model of Cell Death and in Mouse 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine Model of Parkinson's Disease,” Pharmacology 309, (2004): 1067–78.
   Web of Science ®Google Scholar
• A. Iwashita, K. Mihara, S. Yamazaki, S. Matsuura, J. Ishida, H. Yamamoto, K. Hattori, N. Matsuoka, and S. Mutoh, “A New Poly (ADP-Ribose) Polymerase Inhibitor, FR261529 [2-(4-Chlorophenyl)-5-Quinoxalinecarboxamide], Ameliorates Methamphetamine-Induced Dopaminergic Neurotoxicity in Mice,” Pharmacology 310, (2004): 1114–24.
   Web of Science ®Google Scholar
• M. J. Hour, L. J. Huang, S. C. Kuo, Y. Xia, K. Bastow, Y. Nakanishi, E. Hamel, and K. H. Lee, “6-Alkylamino- and 2,3-Dihydro-3′-Methoxy-2-Phenyl-4-Quinazolinones and Related Compounds: Their Synthesis, Cytotoxicity, and Inhibition of Tubulin Polymerization,” Journal of Medicinal Chemistry 43, (2000): 4479–87.
   PubMed Web of Science ®Google Scholar
• Y. Ma, D. Ren, J. Zhang, J. Liu, J. Zhao, L. Wang, and F. Zhang, “Synthesis, Antibacterial Activities Evaluation, and Docking Studies of Some 2-Substituted-3-(Phenylamino)-Dihydroquinazolin-4(1H)-Ones,” Tetrahedron Letters 56, (2015): 4076–79.
   Web of Science ®Google Scholar
• Q. Ding, J. Zhang, J. Chen, M. Liu, J. Ding, and H. Wu, “Tandem Synthesis of 2,3-Dihydroquinazolin-4(1H)-Ones on Grinding Under Solvent-Free Conditions,” Journal of Heterocyclic Chemistry 49, (2012): 375–80.
   Web of Science ®Google Scholar
• A. Maleki, M. Aghaie, N. Ghamari, and M. Kamalzare, “Efficient Synthesis of 2,3-Dihydroquinazolin-4(1H)-Ones in the Presence of Ferrite/Chitosan as a Green and Reusable Nanocatalyst,” International Journal of Nanoscience and Nanotechnology 12, (2016): 215–22.
   Google Scholar
• A. Maleki, T. Kari, and M. Aghaei, “Fe3O4@SiO2@TiO2-OSO3H: An Efficient Hierarchical Nanocatalyst for the Organic Quinazolines Syntheses,” Journal of Porous Materials 24, (2017): 1481–96.
   Web of Science ®Google Scholar
• A. Maleki, M. Aghaei, and N. Ghamari, “Synthesis of Benzimidazolo[2,3-B]Quinazolinone Derivatives via a One-Pot Multicomponent Reaction Promoted by a Chitosan-Based Composite Magnetic Nanocatalyst,” Chemistry Letters 44, (2015): 259–61.
   Web of Science ®Google Scholar
• A. Maleki, M. Rabbani, and S. Shahrokh, “Preparation and Characterization of a Silica-Based Magnetic Nanocomposite and Its Application as a Recoverable Catalyst for the One-Pot Multicomponent Synthesis of Quinazolinone Derivatives,” Applied Organometallic Chemistry 29, (2015): 809–14.
   Web of Science ®Google Scholar
• A. Maleki, M. Aghaei, and T. Kari, “Facile Synthesis of 7-Aryl-benzo[h]tetrazolo[5,1-B]quinazoline-5,6-Dione Fused Polycyclic Compounds by Using a Novel Magnetic Polyurethane Catalyst,” Polycyclic Aromatic Compounds (2017) doi:10.1080/10406638.2017.1325746.
   Web of Science ®Google Scholar
• A. Shabbani, A. Maleki, and H. Mofkhan, “Click Reaction: Highly Efficient Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones,” Synthetic Communications 38, (2008): 3751–59.
   Google Scholar
• X. Zhang, D. Ye, H. Sun, D. Guo, J. Wang, H. Huang, X. Zhang, H. Jiang, and H. Liu, “Microwave-Assisted Synthesis of Quinazolinone Derivatives by Efficient and Rapid Iron-Catalyzed Cyclization in Water,” Green Chemistry 11, (2009): 1881–88.
   Web of Science ®Google Scholar
• A. Alizadeh, R. Ghanbaripour, and L. Zhu, “An Efficient Approach to the Synthesis of Coumarin-Bearing 2,3-Dihydro-4 (1H)-Quinazolinone Derivatives Using a Piperidine and Molecular Iodine Dual-Catalyst System,” Synlett 25, (2014): 1596–600.
   Web of Science ®Google Scholar
• C. Larksarp and H. Alper, “Palladium-Catalyzed Cyclocarbonylation of O-Iodoanilines with Heterocumulenes: Regioselective Preparation of 4 (3H)-Quinazolinone Derivatives,” Journal of Organic Chemistry 65, (2000): 2773–77.
   PubMed Web of Science ®Google Scholar
• A. A. Mohammadi, H. Rohi, and A. A. Soorki, “Synthesis and in Vitro Antibacterial Activities of Novel 2-Aryl-3-(Phenylamino)-2,3-Dihydroquinazolin-4(1h)-One Derivatives,” Journal of Heterocyclic Chemistry 50, (2013): 1129–33.
   Web of Science ®Google Scholar
• A. Maleki, M. Aghaei, H. R. Hafizi-Atabak, and M. Ferdowsi, “Ultrasonic Treatment of CoFe2O4@B2O3-SiO2 as a New Hybrid Magnetic Composite Nanostructure and Catalytic Application in the Synthesis of Dihydroquinazolinones,” Ultrasonics Sonochemistry 37, (2017): 260–66.
   PubMed Web of Science ®Google Scholar
• G. M. Ziarani, Z. K. Asl, P. Gholamzadeh, A. Badiei, and M. Afshar, “The Use of SrFe12O19 Magnetic Nanoparticles as an Efficient Catalyst in the Modified Niementowski Reaction,” Applied Organometallic Chemistry 31, (2017): e3830.
   Web of Science ®Google Scholar
• J. Zhang, J. Liu, Y. Ma, D. Ren, P. Cheng, J. Zhao, F. Zhang, and Y. Yao, “One-Pot Synthesis and Antifungal Activity against Plant Pathogens of Quinazolinone Derivatives Containing an Amide Moiety,” Bioorganic & Medicinal Chemistry Letters 26, (2016): 2273–77.
   PubMed Web of Science ®Google Scholar
• A. Patil, M. Barge, G. Rashinkar, and R. Salunkhe, “Aqueous Hydrotrope: An Efficient and Reusable Medium for a Green One-Pot, Diversity-Oriented Synthesis of Quinazolinone Derivatives,” Molecular Diversity 19, (2015): 435–45.
   PubMed Web of Science ®Google Scholar
• X. Yang, M. Wu, S. Sun, C. Huang, H. Guo, J. Wang, J. Lee, and Y. Xing, “Synthesis of Tricyclic Quinazolinones via Intramolecular Cyclization of 3-(2-Aminoalkyl)-2-(Phenylamino)quinazolin-4(3H)-Ones,” Molecular Diversity 20, (2016): 551–56.
   PubMed Web of Science ®Google Scholar
• T. Magyar, F. Miklós, L. Lázár, and F. Fülöp, “Application of a Ball Milling Technique for the Condensation of Anthranilic Hydrazides with Aromatic Aldehydes Towards 4-Quinazolinone Derivatives,” Chemistry of Heterocyclic Compounds 50, (2015): 1463–69.
   Web of Science ®Google Scholar
• Q. Ding, J. Zhang, J. Chen, M. Liu, J. Ding, and H. Wu, “Tandem Synthesis of 2,3-Dihydroquinazolin-4(1H)-Ones on Grinding Under Solvent-Free Conditions,” Journal of Heterocyclic Chemistry 49, (2012): 375–80.
   Web of Science ®Google Scholar
• A. Maleki, “Fe3O4/SiO2 nanoparticles: An Efficient and Magnetically Recoverable Nanocatalyst for the One-Pot Multicomponent Synthesis of Diazepines,” Tetrahedron 68, (2012): 7827–33.
   Web of Science ®Google Scholar
• A. Maleki, A. A. Jafari, and S. Yousefi, “MgFe2O4/cellulose/SO3H Nanocomposite: A New Biopolymer-Based Nanocatalyst for One-Pot Multicomponent Syntheses of Polysubstituted Tetrahydropyridines and Dihydropyrimidinones,” Journal of the Iranian Chemical Society 14, (2017): 1801–13.
   Web of Science ®Google Scholar
• G. Sorella, G. Strukul, and A. Scarso, “Recent Advances in Catalysis in Micellar Media,” Green Chemistry 17, (2015): 644–83.
   Web of Science ®Google Scholar
• B. H. Lipshutz and S. Ghorai, “Transitioning Organic Synthesis from Organic Solvents to Water. What's Your E Factor?” Green Chemistry 16, (2014): 3660–79.
   PubMed Web of Science ®Google Scholar
• O. Glatter, G. Fritz, H. Lindner, J. Brunner-Popela, R. Mittelbach, R. Strey, and S. U. Egelhaaf, “Nonionic Micelles Near the Critical Point: Micellar Growth and Attractive Interaction,” Langmuir 16, (2000): 8692–701.
   Web of Science ®Google Scholar
• P. Mukherjee, S. K. Padhan, S. Dash, S. Patel, and B. K. Mishra, “Clouding Behaviour in Surfactant Systems,” Advances in Colloid and Interface Science 162, (2011): 59–79.
   PubMed Web of Science ®Google Scholar
• B. Maleki, M. Baghayeri, S. Sheikh, S. Babaee, and S. Farhadi, “One-Pot Synthesis of Some 2-Amino-4H-Chromene Derivatives Using Triethanolamine as a Novel Reusable Organocatalyst under Solvent-Free Conditions and Its Application in Electrosynthesis of Silver Nanoparticles,” Russian Journal of General Chemistry 87, (2017): 1064–72.
   Web of Science ®Google Scholar
• P. Bhattacharyya, S. Paul, and A. R. Das, “Facile Synthesis of Pyridopyrimidine and Coumarin Fused Pyridine Libraries Over a Lewis Base-Surfactant-Combined Catalyst TEOA in Aqueous Medium,” RSC Advances 3, (2013): 3203.
   Web of Science ®Google Scholar
• K. Srinivas and P. K. Dubey, “Triethanolamine: A Resourceful, Reusable, Eco-Friendly, Reaction Medium for Phase Transfer Catalyst – Free Synthesis of 1-(Arylsulfonyl)aryl/heterylmethanes,” Chemical Science Transactions 3, (2014): 375–81.
   Google Scholar
• M. Zhu, X. Wei, B. Li, and Y. Yuan, “Copper-Triethanolamine Complex as Efficient and Active Catalyst for Selective Oxidation of Alkylarenes to Phenyl Ketones by Tert-Butylhydroperoxide,” Tetrahedron Letters 48, (2007): 9108–11.
   Web of Science ®Google Scholar
• P. Zhang, Y. Zhu, Z. Yuan, C. Wu, and H. Tang, “CuBr/PMDETA Combined with Triethanolamine as an Economic and Highly Active Catalyst for Atom Transfer Radical Polymerization,” Journal of Macromolecular Science Part A 54, (2017): 735–41.
   Web of Science ®Google Scholar
• A. U. Khandebharad, S. R. Sarda, C. H. Gill, M. G. Soni, and B. R. Agrawal, “Condition Based Divergence in Synthesis of Tetrahydrobenzo[b]pyrans,” Research on Chemical Intermediates 42, (2016): 5779–87.
   Web of Science ®Google Scholar
• J. A. Molina-Bolívar and C. C. Ruiz, “Micellar Size and Phase Behavior in N-Octyl-β-D-thioglucoside/Triton X-100 Mixtures: The Effect of NaCl Addition,” Fluid Phase Equilibria 327, (2012): 58–64.
   Web of Science ®Google Scholar
• J. B. Gujar, M. A. Chaudhari, D. S. Kawade, and M. S. Shingare, “Sodium Chloride: A Proficient Additive for the Synthesis of Pyridine Derivatives in Aqueous Medium,” Tetrahedron Letters 55, (2014): 6939–42.
   Web of Science ®Google Scholar
• A. Hasseine, A. H. Meniai, and M. Korichi, “Salting-Out Effect of Single Salts NaCl and KCl on the LLE of the Systems (Water + Toluene + Acetone), (Water + Cyclohexane + 2-Propanol) and (Water + Xylene + Methanol),” Desalination 242, (2009): 264–76.
   Web of Science ®Google Scholar
• J. A. Molina-Bolivar, J. Aguiar, J. M. Peula-Garcia, and C. C Ruiz, “Surface Activity, Micelle Formation, and Growth of N-Octyl-Beta-D-Thioglucopyranoside in Aqueous Solutions at Different Temperatures,” Journal of Physical Chemistry B 108, (2004): 12813–20.
   Web of Science ®Google Scholar
• P. Ghosh and A. Mandal, “Sodium Dodecyl Sulfate in Water: Greener Approach for the Synthesis of Quinoxaline Derivatives,” Green Chemistry Letters and Reviews 6, (2013): 45–54.
   Web of Science ®Google Scholar